This series primarily contains personal and family correspondence. In addition, there are legal and financial documents and files related to memberships and affiliations. Correspondents include Holland's Bartow law partner, W.F. Bevis; G.B. "Gabby" Knowles; his wife, Mary Holland; and his brother, Frank Holland. There is also a file pertaining to the genealogy of the Spessard Family. Files are arranged alphabetically.

This series is comprised of chronological files of personal and business papers, including personal correspondence, legislative papers, and legal documents. Although the majority of Holland's legislative files from his tenure in the Florida State Senate can be found in subsequent series within the collection, it should be noted that some legislative correspondence has been intermixed with the personal and business papers found within this series. Files are arranged chronologically.

Chronological files of Holland's correspondence during his term in the State Senate (1932-1940). Files are arranged chronologically by year and then by month.

This series contains the correspondence, legislation, and subject files from Holland's tenure in the State Senate. Of particular interest are files related to the Cross Florida Barge Canal, Alberto Camero and the gambling investigation, the Everglades National Park, communism, the University of Florida, labor issues such as strikes and child labor, and Sen. Robert L. Black's fight with Holland in the Senate. There are numerous files pertaining to chain stores and the Florida Recovery Act, the Florida School Code, taxation, and the citrus industry. Correspondents include several politicians and well-known figures in Florida, including Fred P. Cone, Duncan U. Fletcher, Peter O. Knight, Phil May, Nathan Mayo, Claude Pepper, J. Hardin Peterson, John Ringling, and David Sholtz. Files are arranged alphabetically.

This series primarily is comprised of material pertaining to Holland's campaigns for the Florida Senate. In addition, there is a small amount of papers related to campaigns for election to the U.S. senate, although researchers should note that the majority of the U.S. Senate campaign files are currently housed at Florida State University in Tallahassee. Included in this series are campaign activity files, news clippings, campaign correspondence, mailing lists, lists of key men and women in the state, support correspondence, and congratulatory letters. Files are arranged chronologically. Papers related to the Gubernatorial campaign in 1940 and the U.S. Senate campaign of 1946 can be found in subsequent series within this collection. Although there are no files related to the 1958 primary race against Claude Pepper, there are some political support files pertaining to this race in the Senatorial Papers 85th Congress 2nd Session series. In addition, the Claude Pepper Collection at the Florida State University has several files related to this election.

Correspondence pertaining to the gubernatorial election in 1940. The correspondence deals with campaign support, key men and women in cities and counties, solicitation for appointments to state positions, scheduling appearances, etc. Correspondents include several politicians and well-known figures in Florida, including Charles O. Andrews, Harold Colee, LeRoy Collins, R.A. Gray, Sid Herlong, Phil May, Allen Morris, Claude Pepper, J. Hardin Peterson, A.G. Shands, Bob Sikes, John J. Tigert, and Park Trammell. Other correspondents include family members, friends and business partners including Mary Holland, Frank Holland, W.A. McRae, and W.F. Bevis. There is a special "Colored" file for African American supporters and issues. Files are arranged alphabetically.